1608-11-3

Usage

Uses

Used in Organic Synthesis:
(1Z,3Z)-1,2,3,4-Tetraphenyl-1,3-butadiene is used as a building block for the production of various organic compounds. Its unique structure and reactivity allow it to undergo a wide range of chemical reactions, making it a versatile component in the synthesis of complex organic molecules.
Used in Diels-Alder Reactions:
(1Z,3Z)-1,2,3,4-Tetraphenyl-1,3-butadiene is used as a diene in Diels-Alder reactions, a type of [4+2] cycloaddition. This reaction is a powerful method for constructing six-membered rings and is widely used in the synthesis of natural products, pharmaceuticals, and other organic compounds.
Used in Other Cycloadditions:
In addition to Diels-Alder reactions, (1Z,3Z)-1,2,3,4-Tetraphenyl-1,3-butadiene can also participate in other types of cycloadditions. These reactions can lead to the formation of various heterocyclic compounds and other complex molecular structures, further expanding the utility of (1Z,3Z)-1,2,3,4-Tetraphenyl-1,3-butadiene in organic synthesis.

Upstream product

• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 143-66-8 sodium tetraphenyl borate 
• 501-65-5 diphenyl acetylene 

Relevant academic research and scientific papers

Palladium-catalyzed hydrophenylation of alkynes with sodium tetraphenylborate under mild conditions

(Chemical Equation Presented) In an aqueous solution of acetic acid, PdCl2(PPh3)2 showed high catalytic activity for the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate (NaBPh4) under mild conditions, affording phenyl alkenes in moderate to excellent yields.

ORGANIC CHEMISTRY OF SUBVALENT TRANSITION METAL COMPLEXES XI. OXIDATIVE ADDITIONS OF NICKEL(0) COMPLEXES TO CARBON-CARBON BONDS IN ALKYNES: NICKELIRENES AND NICKELOLES AS CATALYTIC CARRIERS IN THE OLIGOMERIZATION OF ALKYNES

The formation of 2,3,4,5-tetraphenylnickelole-bis(triphenylphosphine) (IIIa) and 2,3,4,5-tetraphenylnickelole-bis(1,2-diphenylphosphino)ethane (IIIb), either from (E,E)-1,2,3,4-tetraphenyl-1,3-butadien-1,4-ylidenedilithium (I) and the corresponding nickel(II) chloride-phosphine complexes (II) or from the reduction of η4-tetraphenylcyclobutadienenickel(II) bromide dimer (XII) in the presence of phosphines, proceeds in good yields.Nickelole IIIa displays physical and chemical properties consistent with its structure and is a catalyst for the trimerization of diphenylacetylene.Nickelole IIIb is a highly associated structure but in its chemical response to alkynes, HOAc, O2, Br2, NaAlEt2H2 and heat displays the properties of a nickelole, rather than a cyclobutadienenickel(0) complex.Attempts to generate IIIb photochemically from η4-1,5-cyclooctadiene(η4-tetraphenylcyclopentadienone)nickel and diphos failed, but it was shown that structural types, such as η4-tetraphenylcyclopentadienone(diphos)nickel (a model for the structure suggested by Hoberg and Richter for IIIb), are unstable.Oligomerizations of diphenylacetylene by bis(1,5-cyclooctadiene)nickel were retarded by conducting the reaction in THF or in the presence of diphos.This retardation permitted the interception of products (cis-stilbene and (E,E)-1,2,3,4-tetraphenyl-1,3-butadiene)diagnostic for the intermediacy of nickelirenes and nickeloles.Deuterium labeling verified the presence of carbo-nickel bonds.These trapping experiments, together with findings on the thermal behavior of nickeloles, are combined into a comprehensive view of the cyclotrimerization, cyclotetramerization and linear polymerization of alkynes by nickel(0).